Winona

She is the Gym leader of the Fortree City and specializes in training Flying Type Pokemon.

Winona is the Fortree City Gym leader; she commands flying type Pokemon. In the anime, Ash arrives in Fortree City looking to challenge Winona, however he finds out that she isn't present. After searching the city he finds her helping out at an annual festival dedicated to flying type Pokemon. Ash battles Winona the next day; after a long battle he recieved the feather badge.